Before They Vanished: The NYC Buildings That Should Never Have Been Destroyed

The concrete jungle.
The city that never sleeps.
The capital of the world.

By whatever name New York City goes, its towering skyline stands proud against the sweeping skies. Who doesn’t recognize those formidable buildings, casting long, dramatic shadows? Who doesn’t dream of walking among giants?

Though they may appear frozen in time—timeless monuments to the city’s greatness, conflicts, and history—New York’s landmarks, like its people, have lived many lives. Some of the most iconic buildings, once bastions of identity, no longer exist. Lost to time and progress, they survive now only in memory and photographs.

Pennsylvania Station

The current Pennsylvania Station sits underground between 7th and 8th Avenues at 31st Street. It is the busiest transit hub in the Western Hemisphere, serving over 600,000 riders daily and acting as a central artery of the city.

When it first opened in 1910, the station looked entirely different—a grand, aboveground landmark that stood as a symbol of architectural ambition. Designed by the acclaimed firm McKim, Mead & White, the original Penn Station was considered a masterpiece of Beaux-Arts design.

In 1963, the city demolished the building to make way for Madison Square Garden, relocating the station underground. The destruction sparked widespread public outrage and mourning for the loss of such a beloved structure. Its demolition became a turning point in the city’s architectural history, leading to the creation of the New York City Landmarks Preservation Commission and galvanizing the city’s preservation movement.

The Crystal Palace

Long before the World’s Fairs of 1939–40 and 1964–65, New York City held its first global exposition: the Exhibition of the Industry of All Nations, in 1853. Built specifically for this event, the city constructed the Crystal Palace next to the Croton Reservoir Distributing Center—an area that would later become Bryant Park. With its lofty, soaring domes, the structure was one of the most awe-inspiring buildings New Yorkers had ever seen.

After the exhibition closed, the Crystal Palace was repurposed as a venue for special events. But tragically, just four years later, a raging fire burned it to the ground—clearing the way for what would eventually become Bryant Park and its beloved winter markets.

The Metropolitan Opera House

Now perhaps more widely known thanks to HBO’s period drama The Gilded Age, the original Metropolitan Opera House was a source of controversy—both when it opened and when it was ultimately demolished. It stood at the heart of a cultural battle between New York’s “new money” and “old money,” directly challenging the Academy of Music’s long-held dominance over the city’s elite arts scene.

Designed by the esteemed architect J. Cleveland Cady, the Met Opera House opened at West 39th Street and Broadway in 1883. However, because Cady had never designed a theater before, many of its features were considered outdated even at the time of its debut. In 1892, a fire destroyed part of the building, prompting a lavish redesign that included the largest proscenium arch in America at the time.

Eventually, the Met outgrew the space, and by 1960, it relocated downtown to the newly constructed Lincoln Center. Despite efforts by theater and opera enthusiasts to preserve the original building and have it designated a historical landmark, the city demolished it in 1967.

Barnum's American Museum

Famous for his traveling circus—and more recently reimagined in a rousing musical starring a handsome, singing, and dancing Hugh Jackman—P.T. Barnum got his start as a museum owner in lower Manhattan. From 1841 to 1865, his museum stood at the corner of Broadway and Ann Street, boasting an ever-changing array of living spectacles and curiosities, ranging from the sensational to the educational.

On July 13, 1865, around noon, the building met its demise in a devastating fire. Newspapers of the time described the pandemonium that filled the smoke-choked streets. Firemen worked frantically to evacuate guests and residents, but tragically, many animals and countless Revolutionary War artifacts were lost to the flames.

Although Barnum attempted to rebuild, the museum never regained its original stature. In 1881, he joined forces with ringmaster James Anthony Bailey and took his show on the rails—forever changing the landscape of American entertainment.

Singer Building – Manhattan, New York

Standing at 647 feet tall, the Singer Building once graced the New York City skyline as the tallest building in the world. Located in Lower Manhattan at the corner of Broadway and Borne Street, the building opened in 1908 and served as the headquarters for the Singer Manufacturing Company. It wasn’t until 1911, when aviator Harry Atwood famously flew around it, that the building gained widespread notoriety.

Its reign didn’t last long. By 1958, the Singer Building had dropped to just the 16th tallest skyscraper in New York City. After years of neglect, it was ultimately demolished in 1968 to make way for the U.S. Steel Building—now known as One Liberty Plaza. The Singer Building went out with a distinction of its own: at the time, it became the tallest building ever intentionally demolished.

The World Building

For many years, the 284-foot spire of Trinity Church was the tallest point in New York City—until architect George Post completed the World Building in 1890. Towering at 99 Park Row and reaching 309 feet, it held the title of tallest building in the world until 1894. Joseph Pulitzer commissioned the structure to serve as the headquarters for The New York World newspaper.

Eager to quite literally look down on his rivals in Newspaper Row, Pulitzer strategically—and perhaps a bit egotistically—placed his office at the very top of the building.

As the city grew and automobiles became essential to its infrastructure, the building was demolished in 1955 to make way for an expanded entrance ramp to the Brooklyn Bridge.